Preheat your oven to 425°F (220°C). Gather your baking sheet, parchment paper, and sharp knife.

Trim off both ends of the delicata squash and slice it in half lengthwise. Scoop out the seeds.

Cut the delicata squash into ½-inch thick slices across the halves.

Spread the squash slices in a bowl or on the parchment-lined baking sheet. Drizzle with olive oil, then add salt and ground black pepper. Toss to coat evenly.

Spread seasoned squash slices in a single layer on the baking sheet. Roast for 15 minutes, flip slices, then roast for an additional 10 minutes until tender and caramelized.

Remove from the oven, let cool slightly, and serve immediately while warm.